Once in a blue moon (and it has been a while) I will watch those makeover shows were a host or team of hosts takes over the wardrobe of one poorly dressed person. Many times, the person is stuck in the past and still wears their college acid washed jeans even though they are pushing the big Five OH. Other times its a stay at home mom who just can't seem to muster up her mojo and now has a wardrobe consisting of tee shirts and sweatpants pilfered from her husband or boyfriend's closet. These folks are easy. All you have to do is remind them how beautiful and amazing they still are regardless of how many pounds gained or how many children birthed. These change-ups (I don't like the term makeover that much) are easy because once the transformation occurs they realize that feeling good about how they look can bring, fun, self confidence and joy into their lives.
Then there are the extremists that, when I see them, my brain wrinkles. You know the ones, the grown women who wear only Orange or don't step out of the house to go anywhere without dressing in the Hello Kitty logo from head to toe. Including underwear. If you ask them why they will say something like, "I love Orange and this is the way I express myself." or "Hello Kitty is my style." I couldn't disagree more. I think they couldn't be farther away from the truth and self expression.
I know, I know - sounds snobbish and so unlike my usual "free to be" philosophy, but here's my take. There is no way you can authentically express YOUR self, if your expression has to be the same day in and day out. without any regard for anything else. That is obsession, not expression. And take it from me and my therapist - the two are not friends.
Expression: I am going to wear my white mini dress with the my pink Hello Kitty Stilettos today. Maybe I will poof my hair and thrown on my red headband.
Obsession: I am going to wear my white shirt with the Hello Kitty print. I am going to wear my Hello Kitty Logo pants with the matching Hello Kitty Socks. I am going to wear my black patent leather shoes that say, "Hello Kitty" in Silver Glitter. To top it all off I am going to put on my Hello Kitty hat, Hello Kitty glitter Tattoo art on my cheek and carry my Hello Kitty Umbrella.
Hello Kitty is not the issue. Hello Kitty can absolutely inspire a specific aesthetic or fashion sense. There is are entire communities devoted to Hello Kitty where people from all walks of life share ideas and support each other's self-expression. I think that is cool and fun. But if everyday is Halloween, no one one wants you on their team at work or you are no longer invited to dinner parties, then Houston, we have a problem.
If you MUST wear the same thing day in and day out regardless of circumstances or environment that is obsessive not expressive. Self expression is fluid and adaptable, bending or changing in response to inspiration and or circumstances. We are complex beings that are in no ways the same day in and day out. Every day life brings different experiences and inspiration that we respond to on some level. Self expression is not rigid and immovable, but obsession is.
I knew a women who's career goal was to score a well paying corporate administrative job.
However, in the summer she would wear her madras shorts and flat sandals to interviews. She was consistently surprised that she never got a call back. She balked at my suggestion to wear a suit or nice dress to at least get in the door. "Why should I wear something I don't like just to impress someone?! They should see me for me!" Here's the thing. Well two things. 1) They did see her for her. They saw a woman so inflexible she wouldn't change into a skirt for a job interview. 2) It is illogical to believe that in the whole entire universe you can't find one interview worthy get-up you like as much as madras shorts. We become obsessive when we are so rigid in our "style" that it hurts us.
Self expression propels us forward while obsession diminishes our quality of life. If your life is being stifled in one way or another because of your "style", than it's time to reevaluate.
Why? Because our clothes don't just hop on our bodies the way fleas hop on a dog. Dogs don't choose fleas. But people choose clothes. And like it or not our choices speak. We use our 5 senses to interpret and assess the world around us, so until we all sharpen our telepathy skills, what you choose to show communicates something about who you are. So if you wear only Hello Kitty every day of your life, than you will not be taken seriously. After all, if you only show us Hello Kitty than doesn't that mean Hello Kitty is all you are about? Of course not, but if people consistently assess you incorrectly, you are either in the wrong environment or your self expression does not adequately tell your true story.
No one should adapt to bigotry or prejudice or be judged on the basis of outdated norms. Women don't have to wear skirt suits and high heels anymore. However, you could be the best dressed person in the building, but if you are too black, or too plump, or too working class -you will not get the job as long as a bigot is in charge.
Clothing can be one of the most intimate vehicles of self expression. It is a wonderful thing to look and feel great on your own terms. We just need to take care that we don't confuse obsession with self expression. My Hello Kitty example may be extreme and dramatic, but we obsess in different ways. There are people who will take their families to financial ruin in order wear the so-called latest and greatest. There are those that equate style and beauty with bubble headed-ness and vanity so they purposefully hide their beauty to show who they are not. There are also those women who are afraid to let anyone see them without make-up or in mom jeans or sweats. They will put everything on hold to present a perfect image. Obsessions come in multitude of ways but no matter how it shows up, it always ends up stealing the fun.
But when we Dress to Express - even a trip to our closet can be a mini adventure!
Dress to Express Part III: So What You've Passed Your Prime - Another One is Coming Down the Pike!
Being middle age means just that, being in the middle of life where you can say both, "I remember when ..." and " I can't wait until ..." in the same sentence. Being middle age means you reminisce about the past and strategize about the future. It means you are as far from the beginning as you are to the end. You get the point. 
